| 1 | 5103 | 9/7/19 9:00am | Danehy 1 - Artificial Turf | Cambridge Galaxy | 4 - 0 | Lexington Golden Hawks | |
| 2 | 5105 | 9/14/19 9:00am | PQ (1A) | Belmont G8-1 Blizzard | 1 - 1 | Cambridge Galaxy | |
| 3 | 5108 | 9/21/19 9:00am | Danehy 1 - Artificial Turf | Cambridge Galaxy | 1 - 3 | Wellesley Bolts | |
| 4 | 5111 | 9/28/19 9:00am | Spy Pond Field | Arlington Wolves | 0 - 1 | Cambridge Galaxy | |
| 5 | 5113 | 10/5/19 9:00am | Danehy 1 - Artificial Turf | Cambridge Galaxy | 1 - 0 | Winchester United | |
| 6 | 5118 | 11/3/19 10:30am | Lincoln Fields2 | Lexington Golden Hawks | 0 - 5 | Cambridge Galaxy | |
| 7 | 5121 | 10/19/19 9:00am | Danehy 1 - Artificial Turf | Cambridge Galaxy | 1 - 1 | Belmont G8-1 Blizzard | |
| 8 | 5122 | 10/26/19 9:00am | Sprague 2 (turf) | Wellesley Bolts | 3 - 1 | Cambridge Galaxy | |
| 9 | 5125 | 11/2/19 9:00am | Danehy 1 - Artificial Turf | Cambridge Galaxy | 0 - 0 | Arlington Wolves | |
| 10 | 5130 | 11/9/19 9:00am | Ryan Connolly Field 11v11 | Winchester United | 1 - 1 | Cambridge Galaxy | |
